Showing metabocard for DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007518)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:38:58 UTC
Update Date2020-05-21 16:28:03 UTC
BMDB IDBMDB0007518
Secondary Accession Numbers
  • BMDB07518
Metabolite Identification
Common NameDG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0), also known as 1,2-di(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycerol or DAG(20:4/20:4), belongs to the class of organic compounds known as 1,2-dg(20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)/0:0)s. These are dg(20:4(5z,8z,11z,14z)/20:4(5z,8z,11z,14z)/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) exists in all eukaryotes, ranging from yeast to humans. DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycerolChEBI
1,2-Di-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycerolChEBI
1,2-Di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolChEBI
DAG 20:4(omega-6)/20:4(omega-6)/0:0ChEBI
DAG(20:4/20:4)ChEBI
DAG(20:4N6/20:4N6)ChEBI
DAG(20:4W6/20:4OMEGA6)ChEBI
DAG(40:8)ChEBI
DG(20:4/20:4)ChEBI
DG(20:4/20:4/0:0)ChEBI
DG(20:4N6/20:4N6)ChEBI
DG(20:4W6/20:4OMEGA6)ChEBI
DG(40:8)ChEBI
Diacylglycerol(20:4/20:4)ChEBI
Diacylglycerol(20:4n6/20:4n6)ChEBI
Diacylglycerol(20:4W6/20:4omega6)ChEBI
Diacylglycerol(40:8)ChEBI
DiarachidonoylglycerolChEBI
DiglycerideHMDB
1,2-Diarachidonoyl-rac-glycerolHMDB
DiacylglycerolHMDB
1,2-Di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycerolHMDB
DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC43H68O5
Average Molecular Weight664.997
Monoisotopic Molecular Weight664.506675286
IUPAC Name(2S)-1-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C43H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-42(45)47-40-41(39-44)48-43(46)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,41,44H,3-10,15-16,21-22,27-28,33-40H2,1-2H3/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t41-/m0/s1
InChI KeyFVXRWZPVZULNCQ-ZPRYGCIXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.67ALOGPS
logP12.66ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity213.44 m³·mol⁻¹ChemAxon
Polarizability81.48 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-2179234000-be6aa1fffed69c8df3bfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-090a-1049015000-8902ef569f14dc437714View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ts-3098443000-16d03c667852a283fe6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052n-2095451000-80ed1234966e2baa0e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-114r-0049003000-0099a085b98b1ce9b25eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1049001000-4c62ee6ed33d69d7992bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3049000000-a211261d91fa213a047aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-b2e0515299b50695a3aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-b2e0515299b50695a3aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0009001000-94d30773d23d1d6beb8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-19764e10c451fc22ee44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0008009000-cf794dff2bfd5d2e0bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0008009000-0d4f260a63ae275f92c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5045069000-17b2142db8bd54efcf71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3097041000-2cbb4094e6d32ffe7e0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-0295020000-7bc3137f39a1bfd02f6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019008000-4dc7730a6a4fa7323c33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-4029000000-0f7ce59496357bcd5b7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4049000000-ac1370945580f701ca18View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007518
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543872
PDB IDNot Available
ChEBI ID77125
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))details
Enzyme Details
2. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails